Article ID Journal Published Year Pages File Type
1373305 Bioorganic & Medicinal Chemistry Letters 2009 4 Pages PDF
Abstract

We describe (i) a simple method for the synthesis of C5-modified nucleosides from 5-iodo-2′-deoxyuridine and (ii) their activity against six types of human cancer cell lines (HCT15, MM231, NCI-H23, NUGC-3, PC-3, ACHN). We generated nitrile oxides in situ from oximes using a commercial bleaching agent; their cycloadditions with 5-ethynyl-2′-deoxyuridine yielded isoxazole derivatives possessing activity against the cancer cell lines. We synthesized several azides from benzylic bromides and their click reactions with 5-ethynyl-2′-deoxyuridine provided triazole derivatives.

Graphical abstractC5-Modified nucleosides with anticancer activity were designed and synthesized by [3+2] cycloaddition. The nucleosides were tested against six different cancer cell lines. The triazole nucleosides which we synthesized through click chemistry exhibit much lower toxicity unlike their isoxazole congeners.Figure optionsDownload full-size imageDownload as PowerPoint slide

Related Topics
Physical Sciences and Engineering Chemistry Organic Chemistry
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